Reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[F:11][C:12]1[CH:18]=[CH:17][C:15]([O-:16])=[CH:14][C:13]=1[C:19]([F:22])([F:21])[F:20].[K+].CC(C)([O-])C.[K+]>C1COCC1>[F:11][C:12]1[CH:18]=[CH:17][C:15]([O:16][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)=[CH:14][C:13]=1[C:19]([F:20])([F:21])[F:22]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of 4-fluoronitrobenzene (2.0 mmol) in anhydrous THF (5 mL) at 0° C., a 1M solution of a potassium 4-fluoro-3-trifluoromethyl-phenoxide (2.2 mmol) in THF (may be generated by adding the corresponding alcohol to a 1M solution of potassium t-butoxide in THF) was added dropwise and under a nitrogen stream, according to General Procedure L1. The reaction mixture was stirred at 0° C. until completion, as indicated by TLC or HPLC. The solvent was then removed in vacuuo and the reaction mixture was treated with cold H2O (15 mL), and extracted with EtOAc (2×15 mL). The combined organic layers were washed with brine and dried over sodium sulfate. Evaporation of the solvent in vacuuo afforded the desired 1-fluoro-4-(4-nitrophenoxy)-2-(trifluoromethyl)benzene. The crude product could be used directly for further transformation.
Workup
- customat 0° C.
- additionwas added dropwise and under a nitrogen stream
- customThe solvent was then removed in vacuuo
- additionthe reaction mixture was treated with cold H2O (15 mL)
- extractionextracted with EtOAc (2×15 mL)
- washThe combined organic layers were washed with brine
- dry with materialdried over sodium sulfate
- customEvaporation of the solvent in vacuuo
Sources & evidence
- ORD record
- ord-5ce5221e831d43c88ea0dc9bb2a3cfd1
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07737285B2
Linked notes
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